Diastereo and Enantioselective Synthesis of 1,2-Diols Promoted by Electrophilic Selenium Reagents

Abstract

Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO 3 H generated “in situ” by oxidation of (PhSe) 2 with (NH 4 ) 2 S 2 O 8 at reflux in a 3:1 mixture of MeCN-H 2 O. Interestingly the reaction can be performed in “one pot” using a catalytic amount of diselenide affording the corresponding diols ( 5 and 6 ) with good yield and good level of diastereo- and enantioselectivity.